Synthesis of Cadinanolide Type of Tricyclicα-Methylene-γ-lactone Using Intramolecular Cyclization ofα-Trimethylsilylmethyl-α,β-Unsaturated Ester with Cyclic Ketone
作者： Chiaki Kuroda , Kunihito Ito
DOI: 10.1246/BCSJ.69.2297
关键词: Methylene 、 Stereochemistry 、 Tricyclic 、 Acrylate 、 Cyclic ketone 、 Chemistry 、 Lewis acids and bases 、 Lactone 、 Stereoselectivity 、 Intramolecular cyclization 、 General chemistry
摘要: Fluoride-promoted intramolecular cyclization of ethyl 6-(2-oxocyclohex-1-yl)-2-(trimethylsilylmethyl)hex-2-enoate afforded 2-(1-hydroxybicyclo[4.4.0]decan-2-yl)acrylate as the major product, together with tricyclic α-methylene-γ-lactone, a model compound cadinanolides. The former product was also converted to γ-lactone. reaction promoted by TiCl4 gave hydroxy ester and its dehydrated product. Both Lewis acid- fluoride-promoted cyclizations trans-decaline system mainly. This stereoselectivity is completely different from that Reformatsky observed Dreiding co-workers.
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